# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_IM01
_database_code_depnum_ccdc_archive 'CCDC 1496203'
_audit_update_record             
;
2016-07-26 deposited with the CCDC.
2017-02-22 downloaded from the CCDC.
;

_audit_creation_date             2015-05-11T20:14:17-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14  H10  N2  O1  Se1'
_chemical_formula_sum            'C14 H10 N2 O Se'
_chemical_formula_weight         301.2

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.5390(4)
_cell_length_b                   8.1345(6)
_cell_length_c                   13.8742(9)
_cell_angle_alpha                94.771(3)
_cell_angle_beta                 98.816(4)
_cell_angle_gamma                93.294(4)
_cell_volume                     614.04(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    24
_cell_measurement_theta_min      2.519
_cell_measurement_theta_max      25.683
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             300
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.045
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_number            18139
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.519
_diffrn_reflns_theta_max         25.683
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_coverage         0
_reflns_number_total             2322
_reflns_number_gt                1880
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0355P)²+0.2386P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2322
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0719
_refine_ls_wR_factor_gt          0.0663
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.049

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.96201(6) 0.34276(3) 0.82725(2) 0.06388(14) Uani 1 1 d . . . . .
N2 N 0.5055(3) 0.2295(2) 0.56928(15) 0.0414(4) Uani 1 1 d . . . . .
O1 O 0.2226(4) 0.0486(3) 0.69463(17) 0.0747(6) Uani 1 1 d . . . . .
N1 N 0.8677(4) 0.3741(3) 0.62137(16) 0.0504(5) Uani 1 1 d . . . . .
C9 C 0.8772(4) 0.5629(3) 0.86047(17) 0.0445(6) Uani 1 1 d . . . . .
C4 C 0.6956(4) 0.3240(3) 0.54283(19) 0.0443(6) Uani 1 1 d . . . . .
C2 C 0.5600(4) 0.2211(3) 0.66992(18) 0.0454(6) Uani 1 1 d . . . . .
C3 C 0.7829(4) 0.3122(3) 0.69728(19) 0.0473(6) Uani 1 1 d . . . . .
C8 C 0.3089(4) 0.1646(3) 0.5020(2) 0.0531(7) Uani 1 1 d . . . . .
H8 H 0.1823 0.1017 0.5214 0.064 Uiso 1 1 calc R U . . .
C6 C 0.4916(5) 0.2884(3) 0.3786(2) 0.0582(7) Uani 1 1 d . . . . .
H6 H 0.4838 0.3073 0.313 0.07 Uiso 1 1 calc R U . . .
C5 C 0.6869(5) 0.3534(3) 0.44458(19) 0.0529(6) Uani 1 1 d . . . . .
H5 H 0.8128 0.4164 0.4248 0.063 Uiso 1 1 calc R U . . .
C1 C 0.4112(5) 0.1318(3) 0.7262(2) 0.0582(7) Uani 1 1 d . . . . .
H1 H 0.4639 0.1381 0.7935 0.07 Uiso 1 1 calc R U . . .
C7 C 0.3015(5) 0.1930(3) 0.4078(2) 0.0587(7) Uani 1 1 d . . . . .
H7 H 0.1692 0.1491 0.3615 0.07 Uiso 1 1 calc R U . . .
C14 C 1.0012(6) 0.6980(4) 0.8338(2) 0.0651(8) Uani 1 1 d . . . . .
H14 H 1.1272 0.6835 0.7972 0.078 Uiso 1 1 calc R U . . .
C12 C 0.7616(7) 0.8784(4) 0.9156(2) 0.0757(9) Uani 1 1 d . . . . .
H12 H 0.7251 0.9848 0.9357 0.091 Uiso 1 1 calc R U . . .
C10 C 0.6926(6) 0.5876(4) 0.9141(2) 0.0676(8) Uani 1 1 d . . . . .
H10 H 0.6054 0.4972 0.9323 0.081 Uiso 1 1 calc R U . . .
C11 C 0.6350(7) 0.7456(4) 0.9415(3) 0.0814(10) Uani 1 1 d . . . . .
H11 H 0.5089 0.7612 0.9777 0.098 Uiso 1 1 calc R U . . .
C13 C 0.9400(7) 0.8560(4) 0.8609(3) 0.0790(10) Uani 1 1 d . . . . .
H13 H 1.0224 0.9471 0.8412 0.095 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 C3 1.910(2) . ?
Se1 C9 1.915(2) . ?
N2 C8 1.370(3) . ?
N2 C4 1.381(3) . ?
N2 C2 1.391(3) . ?
O1 C1 1.213(3) . ?
N1 C3 1.340(3) . ?
N1 C4 1.351(3) . ?
C9 C10 1.368(4) . ?
C9 C14 1.369(4) . ?
C4 C5 1.398(4) . ?
C2 C3 1.386(3) . ?
C2 C1 1.428(4) . ?
C8 C7 1.341(4) . ?
C8 H8 0.93 . ?
C6 C5 1.356(4) . ?
C6 C7 1.401(4) . ?
C6 H6 0.93 . ?
C5 H5 0.93 . ?
C1 H1 0.93 . ?
C7 H7 0.93 . ?
C14 C13 1.385(4) . ?
C14 H14 0.93 . ?
C12 C13 1.347(5) . ?
C12 C11 1.357(5) . ?
C12 H12 0.93 . ?
C10 C11 1.378(4) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
C13 H13 0.93 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 Se1 C9 97.81(10) . . ?
C8 N2 C4 121.8(2) . . ?
C8 N2 C2 131.4(2) . . ?
C4 N2 C2 106.83(19) . . ?
C3 N1 C4 105.0(2) . . ?
C10 C9 C14 118.7(3) . . ?
C10 C9 Se1 119.8(2) . . ?
C14 C9 Se1 121.5(2) . . ?
N1 C4 N2 111.1(2) . . ?
N1 C4 C5 130.0(2) . . ?
N2 C4 C5 118.9(2) . . ?
C3 C2 N2 104.4(2) . . ?
C3 C2 C1 130.9(3) . . ?
N2 C2 C1 124.7(2) . . ?
N1 C3 C2 112.7(2) . . ?
N1 C3 Se1 122.29(18) . . ?
C2 C3 Se1 124.9(2) . . ?
C7 C8 N2 119.1(2) . . ?
C7 C8 H8 120.5 . . ?
N2 C8 H8 120.5 . . ?
C5 C6 C7 121.0(3) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C6 C5 C4 118.8(2) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
O1 C1 C2 126.1(3) . . ?
O1 C1 H1 116.9 . . ?
C2 C1 H1 116.9 . . ?
C8 C7 C6 120.5(3) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C9 C14 C13 120.3(3) . . ?
C9 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C13 C12 C11 120.0(3) . . ?
C13 C12 H12 120 . . ?
C11 C12 H12 120 . . ?
C9 C10 C11 120.4(3) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C12 C13 C14 120.3(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?

